Potassium bis(trimethylsilyl)amide

Base Information

• Chemical Name: Potassium bis(trimethylsilyl)amide
• CAS No.: 40949-94-8
• Deprecated CAS: 114089-96-2,1637383-71-1,1221402-19-2
• Molecular Formula: C6H19KNSi2
• Molecular Weight: 199.485
• Hs Code.: 29319090
• European Community (EC) Number: 424-100-2,609-880-6
• DSSTox Substance ID: DTXSID00390655
• Nikkaji Number: J409.287B
• Wikipedia: Potassium_bis(trimethylsilyl)amide
• Wikidata: Q903636
• Mol file: 40949-94-8.mol

Synonyms:Potassium bis(trimethylsilyl)amide;40949-94-8;KHMDS;Potassium Hexamethyldisilazide;Hexamethyldisilazane potassium salt;potassium;bis(trimethylsilyl)azanide;Potassium hexamethyldisilyl azide;Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt (1:1);MFCD00010330;potassium bis-trimethylsilylamide;potassium bis-(trimethylsilyl)amide;Potassium Bis(trimethylsilyl)azanide;potassiumbis(trimethylsilyl)amide;Hexamethyldislazane Potassium Salt;potassiumhexamethyldisilazide;potasium hexamethyldisilazide;potassium hexamethyldislazane;SCHEMBL2038;potassium hexamethyidisilazide;potassium hexamethyl disilazide;potassium hexamethyl-disilazide;potassium bistrimethylsilylamide;potassium hexamethyldisilazanide;potassium bistrimethylsilyl amide;potassium bis(trimethylsily)amide;potassium bis(trimethysilyl)amide;DTXSID00390655;IUBQJLUDMLPAGT-UHFFFAOYSA-N;potassium bis(trimethylsily) amide;potassium di-(trimethylsilyl)amide;[bis(trimethylsilyl)amino]potassium;potassium bis (trimethylsilyl)amide;potassium bis(trimethylsilyl) amide;potassium bis(trimethylsilyl)-amide;Potassium bis (trimethylsilyl) amide;potassium bis-(trimethylsilyl)-amide;AKOS015909125;potassium N,N-bis(trimethylsilyl)amide;s13925;Potassium bis(trimethylsilyl)amide, 95%;BP-12745;BP-21018;Potassium hexamethyldisilazane 20% in THF;Potassium hexamethyldisilazane, 1M in THF;FT-0605922;H0893;P2730;potassium 1,1,1,3,3,3-hexamethyl-disilazane;1,1,1,3,3,3-hexamethyldisilazane potassium salt;A825360;Potassium bis(trimethylsilyl)amide 11% in toluene;Q903636;Potassium bis(trimethylsilyl)amide, 15 wt. % in toluene;Potassium Bis(trimethylsilyl)amide (14% in Toluene, ca. 0.6mol/L);3-(5-(Pyridin-4-ylmethyl)-5H-cyclopenta[1,2-b:5,4-b']dipyridin-5-yl)cyclohexanone

Chemical Property of Potassium bis(trimethylsilyl)amide

Chemical Property:

• Appearance/Colour: Colorless to amber solution
• Vapor Pressure: 54 mm Hg ( 25 °C)
• Melting Point: 194-195°C
• Refractive Index: 1.4920
• Boiling Point: 126 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 3.24000
• Density: 0.877 g/cm³
• LogP: 2.42250
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with terahydrofuran, ether, benzene and toluene.
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 199.06148413
• Heavy Atom Count: 10
• Complexity: 80.9

Purity/Quality:

99% ^*data from raw suppliers

PotassiumBis(trimethylsilyl)amide(0.5MTolueneSolution) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F
• Hazard Codes: C,F,Xn
• Statements: 14-34-67-65-63-48/20-11-40-36/37/38-19-37
• Safety Statements: 26-36/37/39-45-62-43-46-16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)[N-][Si](C)(C)C.[K+]
• Uses: Potassium bis(trimethylsilyl)amide is a strong base used in the alkylation carbonyl compounds.1 Potassium Hexamethyldisilazide is widely used as a Sterically Hindered Base for Enolate Generation in Selective Formation of Linear Conjugated Dienolates and Alkyl (Z)-3-Alkenoates. Potassium Bis(trimethylsilyl)amide (1M in THF) is used in the preparation of 5-azacytidine, an antineoplastic drug. Also applied in the preparation of β3-AR agonists used in anti-stress formulations. It is also used as a reagent in the preparation of lanthanide complexes employed in selective cyclization reactions.

Technology Process of Potassium bis(trimethylsilyl)amide

There total 6 articles about Potassium bis(trimethylsilyl)amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

lithium bis(trimethylsilyl)amide diethyl etherate (18400-61-8) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium tert-butylate; In benzene; at 20 ℃;

DOI:10.1021/acs.organomet.6b00256

Reference yield:

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 3.25h; Irradiation;

DOI:10.1080/00397919508011786

Reference yield:

tetrakis(trimethylsilyl)tetrazene (52764-24-6) → potassium hexamethylsilazane (40949-94-8)

Guidance literature:

With potassium; In diethyl ether; at 25 ℃; for 1h;

upstream raw materials:

tetrakis(trimethylsilyl)tetrazene

1,1,1,3,3,3-hexamethyl-disilazane

hexamethyldisilazan

lithium bis(trimethylsilyl)amide diethyl etherate

Downstream raw materials:

Potassium; 2,3,4-trimethyl-naphthalen-1-olate

1,1,1,3,3,3-hexamethyl-disilazane

Potassium; (1aR,7R,7aR)-1a,7,7a-trimethyl-2-oxo-1a,2,7,7a-tetrahydro-1-oxa-cyclopropa[b]naphthalen-7-olate

kalium-N,N'-bis(trimethylsilyl)benzamidinat

Refernces

• 1、 Ahman,Somfai. "An efficient preparation of potassium bis(trimethylsilyl)amide (KHMDS)". . p. 2301 - 2303. Retrieved 1995.
• 2、 Chiu, Hsin-Chun,Pearce, Adam J.,Dunn, Peter L.,Cramer, Christopher J.,Tonks, Ian A.. "β-Oxo-δ-diimine Nickel Complexes: A Comparison of Tautomeric Active Species in Ethylene Polymerization Catalysis". supporting information. p. 2076 - 2085. Retrieved 2016/07/07.
• 3、 Prakash, G.K. Surya,Shao, Nan,Wang, Fang,Ni, Chuanfa. "Preparation of α-Fluorobis(phenylsulfonyl)methane (FBSM)". . p. 130 - 144. Retrieved 2014/04/03.